Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita

Abstract

A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L(-1), which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the molecule. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L(-1) for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress.

Metabolic engineering of Escherichia coli for the production of cinnamaldehyde

“…Nematicides are chemical pesticides that eliminate parasitic nematodes on plants. They can be employed with success, although currently there are several disadvantages: (i) it is necessary to pay particular attention to the chemical pesticide used in many susceptible plants and crops, (ii) non-selectivity of the pesticide may occasionally cause elimination of other organisms in addition to nematodes, and (iii) if the pathogen remains after treatment, the damage may be severely exacerbated [ 8 , 9 ]. To substitute for current agricultural chemicals, natural pesticides, which are derived from plants and microbes, have been researched and developed intensively.…”

Novel bisthioether derivatives containing a 1,3,4‐oxadiazole moiety: design, synthesis, antibacterial and nematocidal activities

“…To assess the nematocidal activity of the target compounds 4a-4t against C. elegans, an acute toxicity bioassay was performed following the reported method with some modifications. 49 All target compounds were dissolved in dimethyl formamide (DMF) and diluted with sterile distilled water to obtain stock solutions of double the treatment concentrations of 100 and 50 μg mL -1 . Then, 10 μL of an aqueous suspension containing ∼ 50 living C. elegans was added to a 1 cm diameter Petri dish and treated with 200 μL of the above solution.…”

Synthesis and Anti‐inflammatory Activity of Some New 1,2,3‐Benzotriazine Derivatives Using 2‐(4‐Oxo‐6‐phenylbenzo[d][1,2,3]triazin‐3(4H)‐yl)acetohydrazide as a Starting Material

“…For example, azinphos‐methyl and azinphos‐ethyl are widely used broad‐spectrum insecticides and acaricides in crop protection . 1,2,3‐Benzotriazine derivatives bearing 2‐cyanoiminothiazolidin‐4‐one moieties had significant inhibitory activities against Meloidogyne incognita , which can be utilized as lead compounds . 1,2,3‐Triazine represents a widely used lead structure with multitude of interesting applications in the numerous pharmacological fields; thus, various pharmacological activities have been reported and explored till date .…”

“…In connection with our program work on pyrimidine of expected anti‐inflammatory activity, we tried to synthesize new fused substituted benzotriazinones of expected biological activity. Numerous publications have appeared describing the synthesis of 1,2,3‐benzotriazines possessing a variety of pharmacological activities, such as anti‐inflammatory activity , cardiovascular activity , central nervous system activity , and antimicrobial activities . On the other hand, the prepared 1,2,3‐triazine compounds showed antitumor activity, partly by increasing free radicals production and partly by depletion of intracellular catalase, glutathione peroxidase, glutathione reductase, and reduced glutathione.…”